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Abstract:
Annulative π-extension chemistry provides aconcise synthetic route to polycyclic arenes. Herein, we disclose a nondirected annulation approach of unactivated simple arenes.The palladium-catalyzed 2-fold C−H arylation event facilitates tandem C−C linkage relays to furnish fully benzenoid triphenylene frameworks using cyclic diaryliodonium salts. The inseparable regioisomeric mixture of 1- and 2-methyltriphenylenes is identified by the combined analysis of ion mobility-mass spectrometry, gas-phase infrared spectroscopy, and molecular simulation studies.